Citric Acid → 5-(Furan-3-yl)pyridine-3-carboxylic acid

HRID 454527Notes

Reaction equation

HRID 454527 reaction equation
[OH-].[Na+].[O:3]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([C:14]([O:16]C)=[O:15])[CH:11]=[N:12][CH:13]=2)=[CH:4]1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CO>[O:3]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([C:14]([OH:16])=[O:15])[CH:11]=[N:12][CH:13]=2)=[CH:4]1

Participants

5

Reactant 3

HCID 311Citric AcidHCID 14798Sodium HydroxideHCID 66989989Methyl 5-(furan-3-yl)pyridine-3-carboxylate

Product 1

HCID 639483225-(Furan-3-yl)pyridine-3-carboxylic acidYield 65.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 4 mol/L aqueous solution of sodium hydroxide (2.0 mL) was added to a methanol (10 mL) solution of methyl 5-(furan-3-yl)pyridine-3-carboxylate (0.54 g) at room temperature, followed by stirring at the same temperature for 2 hours and 50 minutes. A 10% aqueous solution of citric acid (8 mL) was added to the reaction mixture at room temperature, and the solvent was evaporated under reduced pressure. Water was added to the obtained residue, and the solid substance was collected by filtration to obtain 0.33 g of 5-(furan-3-yl)pyridine-3-carboxylic acid as a light yellow solid.

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. additionWater was added to the obtained residue
  3. filtrationthe solid substance was collected by filtration

Sources & evidence

ORD record
ord-0f5757db9a114f4ea4c086d54b75ce06
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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